Oahu's most expensive homes

By Treena Shapiro

Published: 2013.09.03 07:34 AM

It’s no secret that Honolulu is one of the most expensive cities in which to live, but what kind of home could you swing if money was no object, or even if you could just afford a $65,000- or even $100,000-a-month mortgage payment?

Here are the five priciest listings on Oahu*:

1. 210 N. Kalaheo, Kailua. Listed at just under $25 million, this property is actually two homes—a five-bedroom main residence and a three-bedroom guest house. It’s on the beach, of course.

2. 503 Portlock Road, Hawaii Kai. This seven-bedroom, six-bath home is so exclusive, its address is withheld on websites such as Zillow. It sits on almost two oceanfront acres in Portlock and has a separate one-bedroom nanny apartment. Lucky nanny!Money talk: $23 million.Contact: Melanie Long, 368-0545.MLS: 1212372.
Video tour

3. 61785 Papailoa Road, Haleiwa. The marketing copy for this North Shore home refers to it as a “trophy estate” with 101 feet of beach frontage. The six bedrooms include two separate guest residences, both of which also open to the private pool.

4. 2332 Makiki Heights Drive, Honolulu. This eight-bedroom property is one of the largest estates in metro Honolulu and features Vladimir Ossipoff’s architecture and Mary Philpotts’ interior design. It has a three-bedroom guest house, and there are other lots available for additional structures.

5. 4461 Kahala Avenue, Honolulu. This is one of the few beachfront homes in Kahala on the market—and, at almost $17 million, it’s listed at significantly less than the $25 million it sold for in 1998. It has four bedrooms and seven baths, with staff quarters above the garage. The listinghighlights a chairman’s office and a ladies’ salon.Money talk: $16.95 million.Contact: Patricia Choi, 734-7711.MLS: 1209852.

** According to real estate website Zillow, the two most expensive properties are on the Big Island and Kauai.

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About Our Writer

Rachel Ross is a Realtor at Berkshire Hathaway HomeServices Hawai‘i Realty. Raised in Hawai‘i Kai, she previously worked in public relations and marketing where she assisted some of O‘ahu’s biggest community developers, educators and businesses. She loves connecting people and says that real estate is a form of matchmaking. She is mom to three teenagers and an avid runner, and notes that the hour each day of pavement-pounding is the only teen-angst-free peace and quiet she gets all day. rachelr@bhhshawaii.com